Cheap flights from Orlando to Boston from $99

In general, January is the cheapest month to fly from Orlando to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $126. If you aren’t able to travel during the month of January, then book flights to Boston from Orlando during February instead. Flights to Boston in February, while not as cheap as those in January, still average around $181.

The cheapest day to depart from Orlando to Boston is on a Friday when prices can be found for as low as $284. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $454.

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Orlando to Boston in the evening for as low as $240. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $749 per ticket.

Fly from Orlando to Boston Logan Intl for the best Orlando - Boston Logan Intl flight prices

You are more likely to see cheaper flights to Boston from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $234 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Orlando for as low as $191 on momondo.

There are 4 cabin classes available to choose from on Orlando to Boston flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 48% on your flight if you consider stops on a Orlando to Boston flight.

As of July 2026, prices for Orlando to Boston flights are approximately 103% more expensive when compared to flights at the same time last year.

Southwest and United Airlines are the most popular carriers operating from Orlando to Boston Logan Intl

JetBlue, Delta and Breeze Airways are the top three most popular airlines that fly to Boston from Orlando according to our data. JetBlue is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 7 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

Historically, on average around 23% of flights between Orlando and Boston have experienced a delay on any given week. The average delay length over the past 12 months has been 163 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Delta have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

34 flights are operational daily from Orlando to Boston as of July 2026. The most popular departure time for this route is 1:00PM, with 43% of flights per day taking off in the afternoon.

As of July 2026, 241 flights take off from Orlando and land in Boston each week. The most common flight departure day for this route is Tue, with 19% of weekly flights taking off on this day.